Process for dispersing amino acids

ABSTRACT

A coated proteinaceous material can be produced by contacting the proteinaceous material with de-oiled phospholipids or mixtures thereof containing less than 20% triglycerides. The coating has between 0.1 and 1.5% by weight of the total proteinaceous material, of de-oiled lecithin. The proteinaceous material is hydrophobic, especially amino acids having a hydrophobicity of higher than 1.0 kJ/mol. In particular, the amino acids are leucine, isoleucine, valine, phenylalanine, tryptophan and/or methionine. The coated amino acids can be incorporated into food product and medicaments.

FIELD OF THE INVENTION

The invention relates to a process for coating amino acids and peptidesand for producing dispersible amino acid and peptide preparations. Theinvention also pertains to the coated material thus produced and tonutritional products containing the coated material.

BACKGROUND

Nutritional compositions destined for feeding patients suffering fromcertain deficits or diseases often need to be fortified with specificamino acids or peptides. For example, leucine is an important ingredientfor compositions intended for replenishing muscular tissue, see e.g. WO01/58284. GB-A-2,292,522 discloses a preparation for supporting theimmune system containing, inter alia, methionine, valine, leucine,threonine, phenylalanine, lysine, isoleucine and tryptophan. WO2004/103383 discloses the use of leucine and glycine for the treatmentof chronic wounds.

However, some amino acids have insufficient solubility, wettability,sinkability or dispersibility or a bad taste or a combination thereof.This applies especially to large neutral (hydrophobic) amino acids suchas leucine, isoleucine, valine, phenylalanine, and tryptophan, and tothe sulphur amino acids methionine and cysteine (or cystine). As aconsequence, the production of such compositions is hampered withdissolution problems, and the compositions are poorly accepted becauseof their bad taste.

Prior art methods developed for overcoming this problem includeencapsulation of the amino acids, e.g. using oils or other relativelyhydrophobic materials, optionally combined with lecithins.

JP-A 2-042967 describes coating of amino acids or drugs with an ethanolor acetone solution of glycerol acetate or lecithin as a surfactant,followed by an oil and again the surfactant. U.S. Pat. No. 6,506,422discloses a nutritional formula for PKU patients containing caseinglycomacropeptide as protein source together with free amino acidsincluding Tyr. The amino acids may be encapsulated with edible fats,such as hydrogenated palm oil. EP-A 363,879 suggests to mask the tasteof free amino acids by combining them with candied fruit and a gellingagent such as starch or gums. US-A 2004/0148013 teaches to coat foodmaterial, such as amino acids, with an organic zinc salt and ahigh-melting fat. EP-A 388,237 discloses a coating for amino acidscontaining about 55% sugar, about 40% hardened fat and about 0.6%lecithin.

SUMMARY OF THE INVENTION

The invention provides an improved approach of producing amino acidpreparations of hydrophobic amino acids or peptides, resulting in abetter dispersibility of the amino acids and peptides, and in a betteracceptability of the resulting food products. The low proportion oftriglycerides allows a more effective wetting and dissolution of theparticles. The increased dispersibility and concomitant effects alsoallow a reduction of losses of valuable material during processing.

The invention thus pertains to a process of increasing thedispersibility and/or wettability and/or decreasing the stickability ofproteinaceous material by coating particles thereof with a phospholipidscomposition having a low content of hydrophobic substances such astriglycerides.

The present invention also pertains to coated proteinaceous materialwhich can be obtained using the process of the invention.

Furthermore, the invention concerns a process of producing nutritionalcompositions containing added proteinaceous material, especially aminoacids, in which the coated amino acids or proteins are combined withother food components, including e.g. lipids, carbohydrates, proteins,vitamins, minerals, and optionally further active components. Also, theinvention relates to nutritional products containing the coated aminoacids or proteins.

DETAILED DESCRIPTION OF THE INVENTION

The process according to the invention for producing coated particles ofhydrophobic proteinaceous material, is characterised by contacting theproteinaceous material with a de-oiled phospholipid composition.Preferred embodiments of the processes and products of the invention aresummarized in the appending claims and are further detailed below.

Proteinaceous Material

In the present description “proteinaceous material” is understood as anyproteins, peptides, amino acids, and amino acid esters, which mayfurther contain minor amounts (e.g. less than 25 wt. %, preferably lessthan 5 wt. %) of other material, such as glycosylated proteins,lipoproteins such as proteins conjugated with palmitic or myristic acid,carbohydrates and the like. Such other material is counted asproteinaceous matter for the proteinaceous part only. Preferably, theproteinaceous material comprises at least 80 wt. %, preferably at least90 wt. % of free amino acids, and/or of peptides having a chain lengthof no more than 10 amino acid residues, i.e. less than 20 wt. %preferably less than 10 wt. % of peptides and proteins of more than 10amino acid residues. More preferably, it comprises at least 60 wt. %,especially at least 80 wt. %, more especially at least 95 wt. %, mostpreferably at least 98 wt. % of the sum of free amino acids anddipeptides. In a particular embodiment, the proteinaceous comprises atleast 50 wt. %, preferably at least 75 wt. %, more preferably at least95 wt. % of free amino acids. Especially it consists essentially of freeamino acids only. It is preferred that the proteinaceous material has acrystalline form before coating.

Herein, “free amino acids” mean the amino acids as such, or their saltsor esters, or their N-acylated or N-methylated derivatives, such asN-acetylcysteine or N,N-dimethylglycine. Preferably the free amino acidsare used as such or as their salts.

The amino acids are in particular hydrophobic amino acids, i.e. aminoacids which according to the classification of Eisenburg et al. (FaradaySymp. Chem. Soc. 17: 109-120 (1982)) have a side chain hydrophobicity(SCH) having a positive value. The side chain hydrophobicity accordingto Eisenburg et al. is presented in the table below. The values are inkJ/mol.

TABLE Hydrophobicity of amino acids in kJ/mol Arg Lys Asp Gln Asn GluHis Ser Thr Pro −7.5  −4.6  −3.0  −2.9 −2.7 −2.6 −1.7 −1.1 −0.75 −0.29Tyr Cys Gly Ala Met Trp Leu Val Phe Ile +0.08 +0.17 +0.67 +1.0 +1.1 +1.5+2.2 +2.3 +2.5  +3.1 

Especially suitable for use in the present invention are hydrophobicamino acids having a SCH of above 1.0, i.e. Met, Trp, Leu, Val, Phe andIle. These have a wetting time of more than 120 s, which makesdissolution or dispersion into other food components especiallydifficult. The wettability (wetting time) can be determined using themethod of International IDF Standard 87:1979.

Thus, the proteinaceous material which is coated according to theinvention preferably has a hydrophobicity of higher than 1.0 kJ/mol.This means that the (number) average SCH of all amino acids present assuch or in dipeptides, or—if present—higher peptides, is 1.0. Morepreferably, the average SCH is at least 1.2. In particular, theproteinaceous material comprises at least 25 wt. %, on total proteinbasis, of amino acids selected from Met, Trp, Phe, Leu, Ile and Val,and/or peptides containing at least 50% by number of said amino acids.Alternatively or in addition, preferably at least 50%, especially atleast 60%, of all amino acids present in the proteinaceous material areamino acids have an SCH of at higher than 1.0, and/or at least 40%,especially at least 50%, of all amino acids present in the proteinaceousmaterial are amino acids have an SCH of at higher than 2.0

FIG. 1 illustrates the dramatic effect of the coating method of theinvention on the wettability of amino acids. The results with Tyr, Glyand Ala (left-hand part of the figure) show that sufficientlyhydrophilic amino acids have a short wetting time, and that coating hasno or only a minor effect on the wetting time, and the results with Met,Trp, Leu, Val, Phe and Ile (right-hand part of the figure) show thatcoating of these hydrophobic amino acids drastically reduces the wettingtime, from about 120 s to below 50 s.

In addition to the amino acids as listed in the table, other hydrophobicamino acids, such as methylglycine or dimethylglycine can be coatedsuccessfully by the process of the invention as well. Peptides to becoated using the process of the invention are those which consist for atleast ⅔ of the number of amino acid residues of amino acid having apositive value of their SCH, especially an SCH above 1.0.

The proteinaceous material that is to be coated can be a singlecomponent, e.g. a single crystalline hydrophobic amino acid. It can alsobe a mixture of such components. Furthermore, a mixture of suchhydrophobic components and more polar components can be coated accordingthe invention, in particular, a mixture of between 50 and 90 wt. % ofhydrophobic amino acids, and between 50 and 10 wt. % of one of morecarbohydrates, such as glucose, galactose, lactose, sucrose, maltose ormaltodextrins, more preferably non-reducing carbohydrates such assucrose or trehalose. In another embodiment, it is preferred to coat thehydrophobic proteinaceous components in the substantial absence of polarcomponents, which is defined to be less than 10% polar components.

Phospholipid Composition

A “phospholipid composition” as used herein is any compositioncontaining a substantial proportion of phospholipids as defined below,e.g. at least 40 wt. % or in particular at least 50 wt. %. Thephospholipid composition may further contain lipids other thanphospholipids, including e.g. triglycerides, diglycerides,monoglycerides, fatty acids and glycolipids, carbohydrates and water.However, where weight percentages are given, these are given on a drybasis, i.e. in the assumed absence of water. A practical example of aphospholipid composition is lecithin. The neutral lipids (triglyceridesetc.) and water are usually part of the acetone-soluble fraction oflecithins, whereas the polar lipids (phospholipids, glycolipids) areusually acetone-insoluble. The phospholipids composition is preferablyused as a dispersion in water.

A “de-oiled phospholipid composition” is a phospholipid compositionhaving a reduced proportion of lipids, in particular triglycerides.Preferably, the content of neutral lipids, i.e. triglycerides,diglycerides, monoglycerides and fatty acids, of the de-oiledphospholipid composition is less than 30 wt. %, more preferably lessthan 20 wt. %, most preferably less than 10 wt. %. The triglyceridecontent is preferably less than 20 wt. %, more preferably less than 10wt. %, most preferably less than 5 wt. % of the de-oiled phospholipidcomposition. The phospholipid compositions may also containcarbohydrates, but preferably no more than 20 wt. %, in particularbetween 2 and 10 wt. %, of the de-oiled phospholipids composition.Furthermore, the phospholipid composition may contain glycolipids asdefined below, e.g. between 1 and 50%, especially between 5 and 35 wt. %of the total de-oiled phospholipid composition. The content ofphospholipids in the de-oiled phospholipid composition to be used in theinvention is preferably at least 65 wt. %, more preferably at least 75wt. %, most preferably at least 80 wt. % of the de-oiled phospholipidcomposition. The proportion of phospholipids may also be lower, e.g. atleast 45 wt. % or especially between 55 and 75 wt. %, if the compositionalso contains glycolipids as defined below; in that case, the totalproportion of phospholipids and glycolipids taken together is preferablybetween 70 and 98 wt. %, more preferably between 80 and 95 wt. %.

When disregarding any carbohydrates that may be present, the de-oiledphospholipids composition preferably contains at least 68 wt. % ofphospholipids, more preferably at least 78 wt. % phospholipids, if noglycolipids are present. In the alternative, the total proportion ofphospholipids and glycolipids taken together—disregarding anycarbohydrates—is preferably between 73 and 99 wt. %, more preferablybetween 83 and 96 wt. %. In the latter case, the content of glycolipidsmay be between 1 and 52, in particular between 5 and 37 wt. % of thede-oiled phospholipids composition (phospholipids, glycolipids andneural lipids). The triglyceride content is preferably below 20 wt. %,more preferably below 10 wt. %, especially below 5 wt. %, and thecombined neutral lipid content below, 31, preferably below 20 and morepreferably below 10 wt. % respectively.

For the purpose of the invention, a “phospholipid” is any compoundhaving a phosphate group and at least one long-chain hydrocarbon group,in particular a fatty acid residue (long-chain meaning at least 15carbon atoms). In particular, a phospholipid contains one or twolong-chain hydrocarbon groups on one side of the phosphate group,usually with an interconnecting glyceryl group, and optionally a polargroup at another side of the phosphate group. The phospholipidspreferably comprise one or more of phosphatidylcholine (PC),phosphatidylethanolamine (PE), phosphatidylserine (PS),phosphatidylinositol (PI), optionally phosphatidic acid (PA),phytoglycolipids and phosphosphingolipids including sphingomyelin, i.e.phospholipids in which the diglyceride residue has been replaced by aceramide unit, and which have a choline group, an inositol or othersugar residue or other polar group on the phosphate group. Also suitableare lyso-phospholipids (hydrolysed phospholipids), i.e. phospholipidshaving only one long-chain fatty acid residue per molecule. Thephospholipids may be a single component, e.g. phosphatidylcholine, or,more commonly, a mixture of components.

A “glycolipid”, which may be present in the (de-oiled) phospholipidcomposition, is understood to be a compound containing at least onelong-chain hydrocarbon unit and at least one sugar unit which may alsobe sulphated (“sulpholipid”). Suitable glycolipids include glycosylatedceramides, such as GalCer, GlcCer, LacCer, and the more complexgangliosides, containing a chain of glycosyl residues, one or more whichmay carry a sialyl group.

The phospholipid composition and de-oiled phospholipid composition to beused for coating the amino acids or peptides and/or proteins can be anyfood-grade phospholipid composition or lecithin. Suitable phospholipidcompositions include soy, sunflower, rapeseed or egg or other lecithin,which have a low content of oil (triglycerides or other hydrophobicmaterial). The oil (neutral lipid) content is preferably less than 20wt. %, more preferably less than 10 wt. %, most preferably less than 5%,based on the total weight of the de-oiled phospholipid composition (i.e.on the total of phospholipids, glycolipids, carbohydrates and neutrallipids). The oil content can be determined for example asacetone-soluble material. Thus the phospholipid compositions to be usedaccording to the invention preferably have a content ofacetone-insoluble material of at least 80 wt. %, preferably at least 90wt. %, most preferably at least 95 wt. %. Moreover, the phospholipids tobe used may be a commercially available de-oiled phospholipidspreparation in dry powder, granulated or wax-like form or a dispersionof phospholipids in aqueous media.

The coated proteinaceous material can be characterised by its phosphoruscontent resulting from the phospholipid coating. Thus, the coatedproteinaceous material of the invention has a phosphorus content between0.001 and 0.1 wt. % (on elemental phosphorus), preferably between 0.005and 0.05 wt. %.

Process

The process of the invention can be carried out using conventionalequipment such as pan coaters, fluid bed coaters and the like. Powder ofthe amino acids or peptides is then contacted with a dispersion of thelecithin in a suitable solvent. Suitable solvents include water, inwhich optionally additional components can be dissolved or dispersed.Such additional components include processing aids and buffers,minerals, trace elements, some vitamins, carbohydrates like sucrose orother non-reducing sugars. The concentration of the phospholipids in thesolvent should be between e.g. 1 wt. % and the critical micelleconcentration, which depends on the further constituents and can bedetermined in a manner known to the skilled person. Preferably, thephospholipids concentration is below 15 wt. %, especially between 2 and10 wt. %.

An amount of the dispersion is applied to the final product or aminoacids, which results in a good wettability and dispersibility of thefinal product. The process according the invention can result in acoating or a granulation (when higher amounts of phospholipids arebrought on the product). Typically the content of de-oiled lecithin inthe final product is between 0.05 and 15 wt. %, preferably between 0.1and 5 wt. %. The method of application can comprise spraying, dippingetc. The contact temperature is preferably between 20 and 60° C., morepreferably between 30 and 50° C., preferably for a period of e.g. 5 to60 min, more preferably 10 to 45 min. After spraying or other contactingprocedure, the particles are preferably dried, e.g. in air for 3-30 min,preferably 6-20 min, at a temperature between 60 and 100° C., preferablybetween 70 and 90° C. The dried particles are then conditioned and areready for use in preparing food products.

Nutritional Products

The coated particles can be packed and used as a product which can bedissolved or suspended as such, or in combination with otheringredients, in any food product or drink by the consumer beforeconsumption.

The particles can also be blended with other powdered ingredients, suchas non-hydrophobic amino acids, carbohydrates, proteins including milkpowder or whey powder, vitamins, minerals etc. to manufacture a premix.Such a premix can be packed and used by consumers for preparing a readyto use food product or drink. The premix can also be used for producingsolutions or dispersions on a commercial scale, which can be used in themanufacture of ready to use liquids or of slurries which can bespray-dried. Processes for manufacturing ready to use liquids are knownin the art and may include new mixing steps with other ingredients,homogenisation and heat treatment steps. Methods for spray-dryingliquids are also known in the art.

The coated particles are readily dispersible and wettable and are verystable during storage at room temperature, normal moisture content inthe dark and under conventional atmosphere. They have and improvedsinkability (resistance to floating on or settling from the dispersion).This stability can be further improved by applying methods known in theart, such as packaging under nitrogen and decreasing atmospherichumidity.

The coated amino acids are particularly suitable for fortification ofclinical nutrition, which are complex products. Hence, the inventionalso pertains to nutritional compositions, containing carbohydrates,proteins, vitamins, and/or minerals, and further containing between 0.1and 50% by weight, preferably between 0.5 and 40%, more preferablybetween 2.5 and 25% by weight, of the total of carbohydrates, protein(total proteinaceous material) and lipids, of a coated proteinaceousmaterial as described above. It is preferred that the compositioncontains at least carbohydrates, preferably at least 10% of the caloriccontent of the composition, especially between 25 and 70% of the caloriccontent. If the coated proteinaceous material only contains one or a fewamino acids, it will often be preferred that further protein material ispresent. The total protein (including amino acids) is preferably atleast 5% of the caloric content of the composition, more preferablybetween 10 and 40% of the caloric content. The presence of lipids isalso possible, in particular between 5 and 35% of the caloric content,although the lipid content will often be low, or zero. The compositionmay be a liquid composition, although a dry composition is oftenpreferred. A powdered product constitutes a preferred embodiment of theinvention.

The coated particles and the products containing them can be used as amedicinal or health food or as a supplement, especially for treatingconditions which require the administration of elemental proteincompositions (comprising free amino acids or small peptides rather thanintact proteins), or which require supplementation of specific aminoacids. Where more than one amino acid is to be incorporated in the foodproduct or supplement, at least one, hydrophobic, amino acid is includedin the coated form according to the invention. Other amino acids,especially non-hydrophobic ones, may be added as such, or with aconventional coating, for example using carbohydrates. Alternatively,all amino acids can be combined before coating, and then be coatedaccording to the invention.

As a example, a supplement for phenylketonuria (PKU) patients containinga mixture of amino acids, preferably all amino acids with the exceptionof phenylalanine. At least one of the hydrophobic amino acids, butpreferably all of Ile, Leu, Val, Trp and Met, are incorporated with ade-oiled lecithin coating, while other amino acids are added as such.Alternatively, all amino acids (except Phe) are coated by the process ofthe invention and then incorporated into the supplement.

EXAMPLES Example 1 Amino Acid with Improved Dispersibility for Use asRaw Material

A de-oiled soy lecithin obtained from Cargill Texturizing Solutionscontaining acetone-insoluble material of more than 96%, was dispersed inwater until a final concentration of 5.9 wt. %. An amount of 50 kg 99%pure leucine powder obtained from Rexim was placed in a fluid bedagglomerator, Aeromatic AG obtained from Niro Inc. Fluidisation wasstarted at a bed temperature of 34° C. and the lecithin dispersion wassprayed for 30 min at a rate of 0.143 l/min. The powder was then driedby passing heated air (70° for 10 min. and subsequently cooled to 26° C.Then the agglomerator was stopped, the powder was sieved using a sieveof 2000 μm mesh and filled in bags.

FIG. 2 shows an electron microscopy image (× 200) of leucine powdercoated according to the present example. The wetting times was >120 s.The powder had a good dispersibility in water determined according tothe method of International IDF Standard 87:1979.

Example 2 Dry-blended Powder for Treatment of Children with a MetabolicDisorder

A powder supplement was prepared for the dietary management ofphenylketonuria and hyperphenylalaninemia. The supplement is notnutritionally complete. It contains per 100 g:

Energy 1189 kJ (280 kcal) Amino acids 71.9 g a. hydrophobic amino acidsexcluding phenylalanine 18.6 g (lecithin-coated using process ofexample 1) b. non-hydrophobic amino acids 53.3 g Lipids 0.14 g De-oiledlecithin 0.14 g Carbohydrates 10 g Minerals Na 540 mg K 1200 mg Ca 2300mg Mg 300 mg P 1380 mg Cl 900 mg Fe 30 mg Trace elements Zn 30 mg Cu 2.1mg I 340 μg Mn 3.6 mg Cr 120 μg F 1.8 mg Mo 95 μg Se 50 μg VitaminsVitamin A 1.2 mg Vitamin D₃ 18 μg Vitamin E 21 mg Vitamin K₁ 57 μgVitamin B₁ 1.8 mg Vitamin B₂ 2.4 mg Vitamin B₆ 2.7 mg Niacin 12.6 mgFolic acid 288 μg Biotin 90 μg Vitamin B₁₂ 3.6 μg Pantothenic acid 11.4mg Vitamin C 180 mg Choline 780 mg Myo-inositol 265 mg Other Carnitine150 mg

The product was stable and readily dispersible in water of roomtemperature and had a good taste.

Example 3 Nutritionally Complete Product Enriched with Dry-blended AminoAcid

A nutritionally complete product was prepared for the treatment ofcancer patients at risk of suffering from cachexia. It contains per 100g:

Energy 1794 kJ (428 kcal) Protein 27.0 g a. Milk protein isolate 19.1 gb. Whey protein concentrate 4.94 g c. Leucine (example 1) 2.95 g Lipids[marine oil + vegetable] 14.2 g a. EPA 1.50 g b. DHA 0.72 gCarbohydrates 46.5 g a. sucrose 11.2 g b. maltodextrin 22.5 g c.trehalose 11.2 g d. lactose 1.58 g Fibre 5.4 g a. Fructosaccharide 0.53g b. GOS 4.81 g

The leucine is dry mixed with the powder after spray-drying of anemulsion of the other ingredients. The product was stable and readilydispersible in water of room temperature and had a relatively goodtaste.

The invention claimed is:
 1. A coated proteinaceous material comprisingat least 60 wt. % of the sum of free amino acids and dipeptides, whichproteinaceous material (a) has a hydrophobicity greater than 1.0 kJ/mol,and (b) comprises at least 25 wt. %, on a total protein basis, of: (i)methionine (Met), tryptophan (Trp), phenylalanine (Phe), leucine (Leu),isoleucine (Ile) or valine (Val), and/or (ii) peptides containing atleast 50% by number of Met, Trp, Phe, Leu, Ile or Val; and (c) comprisesa coating comprising between 0.1 and 1.5%, by weight of the totalproteinaceous material, of a de-oiled phospholipid composition thatcontains at least 65 wt % phospholipids and less than 20 wt. %triglycerides as a percentage of dry weight.
 2. The coated proteinaceousmaterial according to claim 1, comprising between 0.001 wt. % and 0.1wt. % phosphorus.
 3. The coated proteinaceous material according toclaim 1, in which the proteinaceous material comprises at least 75 wt.%, on a total protein basis, of free amino acids or their salts.
 4. Thecoated proteinaceous material according to claim 1, in which said wt %of triglycerides in the de-oiled phospholipid composition is less than10 wt. %.
 5. The coated proteinaceous material according to claim 1, inwhich at least 40% of all amino acids present in the proteinaceousmaterial have a side chain hydrophobicity of higher than 2.0 kJ/mol. 6.A nutritional composition, comprising: (i) carbohydrates, proteins,vitamins, and/or minerals, and (ii) the coated proteinaceous materialaccording to claim 1 at a wt %, based on weight of the carbohydrates andproteins, of between 0.1 and 50 wt %.
 7. The nutritional compositionaccording to claim 6, wherein the coated proteinaceous material isbetween 0.5 wt. % and 30 wt. %.
 8. A nutritional composition,comprising: (i) carbohydrates, proteins, lipids, vitamins, and/orminerals, and (ii) the coated proteinaceous material according to claim1 at a wt %, based on weight of said carbohydrates, proteins and lipids,of between 0.1 wt. % and 50 wt. %.
 9. The nutritional compositionaccording to claim 8 wherein the coated proteinaceous material isbetween 0.5 wt % and 30 wt. %.
 10. A process for producing coatedproteinaceous material, the material comprising at least 60 wt. % of thesum of free amino acids and dipeptides, which proteinaceous material (a)has a hydrophobicity greater than 1.0 kJ/mol, and (b) comprises at least25 wt. %, on a total protein basis, of: (i) methionine (Met), tryptophan(Trp), phenylalanine (Phe), leucine (Leu), isoleucine (Ile) or valine(Val), and/or (ii) peptides containing at least 50% by number of Met,Trp, Phe, Leu, Ile or Val; wherein the process comprises contacting theproteinaceous material with a de-oiled phospholipid compositioncomprising less than 20% triglycerides based on total dry weight of thede-oiled phospholipid composition to produce said coated particles. 11.The process according to claim 10, in which the proteinaceous materialcomprises at least 80 wt. % of the sum of free amino acids anddipeptides.
 12. The process according to claim 10, in which theproteinaceous material comprises at least 75 wt. %, on a total proteinbasis, of free amino acids or their salts.
 13. The process according toclaim 10, in which the de-oiled phospholipid composition comprises lessthan 10 wt. % triglycerides.
 14. The process according to claim 10, inwhich the de-oiled phospholipid composition comprises at least 70 wt. %of phospholipids and/or glycolipids.
 15. A process for producing anutritional composition, comprising combining (i) carbohydrate, protein,vitamin, or mineral food components, with (ii) the coated proteinaceousmaterial according to claim 1, thereby producing said nutritionalcomposition.
 16. A process for producing a nutritional composition,comprising combining (i) carbohydrate, protein, vitamin, or mineral foodcomponents with (ii) the coated proteinaceous material according toclaim 2, thereby producing said nutritional composition.
 17. A processfor producing a nutritional composition, comprising combining (i)carbohydrate, protein, vitamin, or mineral food components, with (ii)the coated proteinaceous material produced in accordance with claim 10,thereby producing said nutritional composition.